Hydrochloric Acid → HCID 67343742, compound

HRID 1474420Notes

Reaction equation

HRID 1474420 reaction equation
O.Cl.[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([N+:23]([O-])=O)[CH:17]=3)(=[O:15])=[O:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1.C(OC(=O)C)C>C(O)C.[Fe]>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH2:23])[CH:17]=3)(=[O:15])=[O:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 67345955HCID 67345955, compound

Product 1

HCID 67343742HCID 67343742, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
92.5 °C

Procedure

To a 250 mL round bottomed flask, added Iron powder (1.56 grams, 27.9 mmol), 10 mL demineralized water and heated to 90-95° C. At this temperature, 4 mL of concentrated hydrochloric acid was added drop wise. The mass was further heated at 90-95° C. for 1 hour. Then cooled the mass to 60° C. and added absolute ethanol (25 mL). A solution of 6-chloro-3-(4-methyl-3-nitro benzenesulfonyl)-1H-indole (obtained from above step) (2.8 grams, 7.9 mmol) in 10 mL absolute ethanol was added lot wise over a period of 15 minutes. Then the mass was refluxed for 3 hours at 80° C. The mass was cooled to 25° C., added ethylacetate (200 mL) and stirred for 5 minutes. The reaction mass was then filtered through buckner funnel, washed with ethylacetate (3×50 mL). Aqueous layer separated from the filtrate and the organic layer was washed with brine solution (1×50 mL), dried over anhydrous sodium sulfate and solvent was concentrated to obtain oily mass. The technical product was further purified by column chromatography to obtain the title product, the eluent being 70% ethylacetate and 30% n-hexane. Yield: 1.47 grams

Workup

  1. temperatureThe mass was further heated at 90-95° C. for 1 hour
  2. temperatureThen cooled the mass to 60° C.
  3. temperatureThen the mass was refluxed for 3 hours at 80° C
  4. temperatureThe mass was cooled to 25° C.
  5. filtrationThe reaction mass was then filtered through buckner funnel
  6. washwashed with ethylacetate (3×50 mL)
  7. customAqueous layer separated from the filtrate
  8. washthe organic layer was washed with brine solution (1×50 mL)
  9. dry with materialdried over anhydrous sodium sulfate and solvent
  10. concentrationwas concentrated
  11. customto obtain oily mass
  12. customThe technical product was further purified by column chromatography

Sources & evidence

ORD record
ord-f3b0177bc61c44bf835abac5a167d369
Source dataset
uspto-grants-2015_04
Patent number
US09018231B2

Reaction notes

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